Hydrochloric Acid → 2-Benzylresorcinol

HRID 2272780Notes

Reaction equation

HRID 2272780 reaction equation
[CH2:1]([C:8]1[C:13]([O:14]COC)=[CH:12][CH:11]=[CH:10][C:9]=1[O:18]COC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>CO>[CH2:1]([C:8]1[C:9]([OH:18])=[CH:10][CH:11]=[CH:12][C:13]=1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 251387862-Benzyl-1,3-bis(methoxymethoxy)benzene

Product 1

HCID 6080772-BenzylresorcinolYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 13 (214 mg, 0.74 mmol) in MeOH (6.20 mL) was treated dropwise with 3 M HCl (0.22 mL, 5.92 mmol), then heated to reflux for one hour. Water (10 mL) was added and the solution was extracted with EtOAc (3×15 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), and concentrated to afford 14 as a red amorphous solid (149 mg, 99%). 1H NMR (CDCl3, 400 MHz) δ 7.31 (d, J=6.6 Hz, 4H), 7.25-7.19 (m, 1H), 7.01 (t, J=8.1 Hz, 1H), 6.44 (d, J=8.1 Hz, 2H), 4.82 (s, 2H), 4.09 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. extractionthe solution was extracted with EtOAc (3×15 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afd2f47199474ff9a84e251b4174ea39
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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